Issue 30, 2019

Total synthesis of (+)-ar-macrocarpene

Abstract

This report features the first catalytic asymmetric total synthesis of a sesquiterpene, (+)-ar-macrocarpene (1), in 7 steps with 42.1% overall yields from commercially available inexpensive 5,5-dimethylcyclohexane 1,3-dione. This strategy relies on a key [3,3]-sigmatropic rearrangement effecting reductive transposition through allylic diazene rearrangement (ADR) in a single step from intermediate allylic alcohol (+)-12 under the Mitsunobu reaction conditions with o-nitrobenzenesulfonyl hydrazide (o-NBSH). Enantioselective reduction of α-bromo vinylogous ester 16 under the Corey–Bakshi–Shibata reduction conditions forges the required stereocenter in the allylic alcohol (+)-12 in a highly enantioenriched manner (95% ee).

Graphical abstract: Total synthesis of (+)-ar-macrocarpene

Supplementary files

Article information

Article type
Communication
Submitted
18 juin 2019
Accepted
09 juil. 2019
First published
09 juil. 2019

Org. Biomol. Chem., 2019,17, 7140-7143

Total synthesis of (+)-ar-macrocarpene

A. Khatua, S. Niyogi and V. Bisai, Org. Biomol. Chem., 2019, 17, 7140 DOI: 10.1039/C9OB01373C

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